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Org Biomol Chem ; 9(3): 673-5, 2011 Feb 07.
Article in English | MEDLINE | ID: mdl-21132176

ABSTRACT

An efficient diastereoselective synthesis of (-)-stemoamide has been accomplished from a pyroglutamic acid derivative in eight steps and with 24% overall yield. The synthesis features an intramolecular samarium diiodide-promoted 7-exo-trig cyclization of a ketyl radical generated from the corresponding aldehyde.


Subject(s)
Heterocyclic Compounds, 3-Ring/chemical synthesis , Lactones/chemical synthesis , Cyclization , Free Radicals/chemistry , Molecular Structure , Stereoisomerism
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